The messaging rules are set up. Confirmation goes out, check-in goes out the day before, check-out goes out that morning. Then a guest writes at 4 p.m. on arrival day asking whether they can get in early, and another asks about the dryer in the unit that has a different one. The templates did their job. The questions they cannot answer are still yours.
This article covers two things: how to set up Hospitable's automated messages so they fire when you expect, and what remains for a person or for a reply written from the booking.
What Hospitable's automated messages cover
According to Hospitable's help center (checked 2 October 2026), messaging rules come in two kinds:
- Event messages, triggered when something happens on a reservation: a new inquiry, a new reservation, a cancellation, a payment issue, a special offer.
- Scheduled messages, sent relative to the stay: after a new reservation, before check-in, after check-in, before check-out, after check-out or a review request, or on a given day of the week.
Separately, question rules use detected question topics so a reply can be prepared or sent for common questions at a given stage of the reservation. That is the part closest to answering guests, so it is worth setting up carefully.
How to set them up well
1. Put time-critical details in the New reservation message. Hospitable's last-minute bookings article says event messages fire when the event occurs, even for a last-minute stay. Scheduled messages behave differently. A "Before check-in" rule with "Exclude last-minute bookings" turned on skips anyone who books after the send time. With it off, the help center says the message is sent 30 minutes after booking, which gives you time to review or cancel it. A "Before check-out" message is not scheduled at all if the booking arrives after its send time. Hospitable's own advice is to include essential check-in information in the New reservation message.
2. Decide on "Exclude last-minute bookings" on purpose. Both settings are defensible. What is not is leaving the default unexamined and finding out when a 6 p.m. booking arrives with no access instructions.
3. Scope each rule to platform, host and property. The troubleshooting guide checks scoping first, and it checks it as it was when the message was created, not as it is now.
4. Handle property differences with scoping or custom codes. Per the property-specific messages article, you can copy a rule per property, or create custom codes with the same name for each property and insert the code in one rule. Fewer rules means fewer places for an old instruction to survive.
5. Know what pauses a message. If a guest has an incomplete task, such as a rental agreement or a security deposit, scheduled messages are withheld, per the troubleshooting guide. And a delayed New reservation message is cancelled if you reply to the guest manually before it sends.
6. Set up question rules for the repeat questions. From Hospitable's question replies article: create a rule per topic, write the answer for the stages where it applies (before reservation, before check-in, staying), and scope it to platform, host and property. Skip greetings in the template. The same article says timing is one setting across all question rules, that the default prepares the answer and emails it to you instead of sending, and that the feature is not on the Essentials plan.
7. Check where a message went. The reservation's Activity log shows whether a message was scheduled, sent, cancelled or never created. If the channel was disconnected when a message was due, the message was cancelled and does not resend on reconnect; you send it manually.
What is left after the rules are right
A rule answers a question that has the same answer for every guest at that stage. Wi-Fi, parking, the trash schedule: write them once.
What stays open is the question whose answer depends on this booking and what is happening around it:
- Can we arrive at 1 p.m.? Depends on whether the previous guest has left and the clean is done.
- Can we add a dog? Depends on the unit's rules, the stay's length and what the booking already says.
- The code did not work. Depends on which unit, which lock, which reservation.
Question rules answer by topic. Check which property details your rules include and which requests still need current information or a team decision. In a growing portfolio that person is often you, answering the same shapes of question all week.
Before you tune your rules
- List your last 20 guest messages and mark which a rule could have answered.
- Check "Exclude last-minute bookings" on every scheduled rule.
- Move check-in essentials into the New reservation message.
- Confirm scope on platform, host and property for each rule.
- Look at the Activity log of one real reservation and read it end to end.
How InnSync answers the rest
InnSync runs the operation around the PMS. Carmen, InnSync's AI agent, writes replies from the booking, the unit and your house rules, so an early-arrival question starts from that stay's booking details, not a generic line. When a situation needs a decision, such as an exception, a complaint or an unusual request, she brings in your team. You choose, per channel, whether she replies on her own or drafts for review. InnSync also supports routines around each reservation, such as cleaning confirmation and check-in requirements.
Your Hospitable rules keep doing what they do well. The aim is not to rewrite them. It is to give your team a clear process for requests that still need attention.
If you use Hospitable
Keep Hospitable. InnSync runs the operation around it — the connection is set up with you during onboarding.
During onboarding, we agree which booking details and routines to configure first, alongside your existing Hospitable messaging rules. Next step: see InnSync for Hospitable.